Potassium Cyanide → 2-Fluoro-4-iodobenzonitrile

HRID 1034111

反応式

HRID 1034111 の反応式
N([O-])=O.[Na+].[F:5][C:6]1[CH:12]=[C:11]([I:13])[CH:10]=[CH:9][C:7]=1N.[C-:14]#[N:15].[K+].C(=O)(O)[O-].[Na+].[OH-].[Na+]>S(=O)(=O)(O)O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Cu+2].C1C=CC=CC=1.C(O)(=O)C>[C:14]([C:7]1[CH:9]=[CH:10][C:11]([I:13])=[CH:12][C:6]=1[F:5])#[N:15]

参加物

11

反応物 5

HCID 9032Potassium CyanideHCID 14798Sodium HydroxideHCID 1856942-Fluoro-4-iodoanilineHCID 516892Sodium BicarbonateHCID 23668193Sodium Nitrite

生成物 1

HCID 27745182-Fluoro-4-iodobenzonitrile収率 29.5%

試薬・触媒・溶媒 5

HCID 24463Copper sulfate pentahydrate触媒HCID 176Acetic Acid溶媒HCID 241Benzene溶媒HCID 962Water溶媒2 回HCID 1118Sulfuric Acid溶媒

実験手順

27 g of sodium nitrite was dissolved in 205 ml of sulfuric acid and cooled to 10° C. or less, and then 238 ml of acetic acid was added. At 20° to 25° C., 65 g of 2-fluoro-4-iodoaniline was added to the solution, and then the solution was agitated for one hour. A second solution was made by dissolving 82.5 g of copper sulfate pentahydrate in 20.5 ml of water, to which was added 140 g of ice, and this solution was added to the first. A third solution containing 88 g of potassium cyanide dissolved in 207 ml of water, 500 g of sodium bicarbonate, and 206 ml of benzene was added to the first solution, and a diazonium salt sulfuric acid solution was added therein. After agitation at room temperature for 3 hours, a sodium hydroxide aqueous solution was added to dissolve the crystals. After being extracted with chloroform, the crystals were washed three times alternating with a 10% sodium hydroxide solution and water. After distillation of the chloroform, the residue was extracted with hexane, and the hexane was distilled off. This residue was subjected to vacuum distillation (95° to 110° C./15 mmHg), and further recrystallized to obtain 20 g of 1-cyano-2-fluoro-4-iodobenzene.

後処理

  1. temperaturecooled to 10° C. or less
  2. additionthis solution was added to the first
  3. waitAfter agitation at room temperature for 3 hours
  4. dissolutionto dissolve the crystals
  5. extractionAfter being extracted with chloroform
  6. washthe crystals were washed three times
  7. distillationAfter distillation of the chloroform
  8. extractionthe residue was extracted with hexane
  9. distillationthe hexane was distilled off
  10. distillationThis residue was subjected to vacuum distillation (95° to 110° C./15 mmHg)
  11. customfurther recrystallized

出典と根拠

ORDレコード
ord-6c4afcb0019747d1ab02f0eeafc1bcd1
出典データセット
uspto-grants-1994_05
特許番号
US05314640

関連ノート

読み込み中…